S-Trityl-L-Cysteine → HCID 57562095, Verbindung

HRID 2098226Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2098226
[NH2:1][C@@H:2]([CH2:6][S:7][C:8]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([OH:5])=[O:4].CCN(C(C)C)C(C)C.[F:36][C:37]([F:55])([F:54])[C@H:38](OS(C(F)(F)F)(=O)=O)[C:39]1[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=1>C(Cl)Cl>[F:55][C:37]([F:36])([F:54])[C@@H:38]([NH:1][C@@H:2]([CH2:6][S:7][C:8]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:3]([OH:5])=[O:4])[C:39]1[CH:40]=[CH:41][C:42]([F:45])=[CH:43][CH:44]=1

Komponenten

5

Edukt 3

HCID 76044S-Trityl-L-CysteineHCID 81531DiisopropylethylamineHCID 86610096trifluoromethanesulfonic acid 2,2,2-trifluoro-1(R)-(4-fluorophenyl)ethyl ester

Produkt 1

HCID 57562095HCID 57562095, VerbindungAusbeute 77,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

2(R)-Amino-3-tritylsulfanylpropionic acid (78 g, 214.6 mmol) was dissolved in CH2Cl2 and DIPEA (112 mL, 643.8 mmol) was added and the reaction mixture was stirred for 10 min at room temperature. Trifluoromethanesulfonic acid 2,2,2-trifluoro-1(R)-(4-fluorophenyl)ethyl ester (70 g, 214.6 mmol) in CH2Cl2 was added and the reaction mixture was stirred overnight at room temperature. Solvent was removed under the reduced pressure and the residue was dissolved in Et2O and washed with 1N HCl, brine and dried over MgSO4. Solvent was removed give 2(R)-[2,2,2-trifluoro-1(S)-(4-fluorophenyl)ethylamino]-3-tritylsulfanylpropionic acid (90 g) as a yellow solid.

Aufarbeitung

  1. stirringthe reaction mixture was stirred overnight at room temperature
  2. customSolvent was removed under the reduced pressure
  3. dissolutionthe residue was dissolved in Et2O
  4. washwashed with 1N HCl, brine
  5. dry with materialdried over MgSO4
  6. customSolvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-17f7345a1b6341ddb318b0b81553d5cf
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450373B2

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